I've noticed when editing dgnlibs, that OpenRoads will crash the first time I try to use the dgnlib that I just edited.
For instance, I will open a dgnlib and make a change to a text favorite, save settings in the dgnlib, and move back to the working dgn. If I go in to manage an annotation group that references the updated dgnlib, OpenRoads will crash if I turn on the "Display" checkbox. Similarly, if I go into the Drawing model cut section and use the Annotate Model tool to annotate it with the updated settings, OpenRoads will crash.
However, if I reopen the working dgn and try it again, it will work from then on. For some reason, OpenRoads is crashing on the first attempt to use the edited dgnlib.
I've noticed this when editing text favorites, text styles, annotation groups, annotation definitions, and survey settings, but I presume other dgnlib changes would also cause ORD to crash similarly.